Triethylamine → HCID 59880457, compound

HRID 1682419Notes

Reaction equation

HRID 1682419 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:24])=[C:5]([C:20]([O:22][CH3:23])=[O:21])[C@@H:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:7]=1[C:8]([OH:10])=[O:9].ClC(OCC(C)C)=O.C(N(CC)CC)C.[C:40]([NH:43][CH2:44]CO)(=[O:42])[CH3:41]>O1CCCC1.C(OCC)(=O)C>[C:40]([NH:43][CH2:44][CH2:23][O:22][C:20]([C:5]1[C@H:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:7]([C:8]([OH:10])=[O:9])=[C:2]([CH3:1])[NH:3][C:4]=1[CH3:24])=[O:21])(=[O:42])[CH3:41]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8880AcetylethanolamineHCID 62365Isobutyl chloroformateHCID 748474(4S)-5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid

Product 1

HCID 59880457HCID 59880457, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The authentic (R)-form of the title compound was prepared as follows. That is, 5 mg of (S)-(+)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-3-pyridinecarboxylic acid prepared according to the method described by Shibanuma et al. (Chem. Pharm. Bull., 28(9), 2809-2812 (1980)) was dissolved in 0.5 ml of tetrahydrofuran. Then 2 μl of isobutyl chloroformate was added to the solution. After stirring for 10 minutes, 6 μl of triethylamine and 30 μl of N-acetyl-ethanolamine were added to the mixture followed by stirring for further 2 hours. After 5 ml of ethyl acetate was added to the reaction mixture, the mixture was washed with water and the resulting organic layer was dried over anhydrous sodium sulfate. The solvent was then distilled off. The residue thus obtained was purified on a preparative silica gel TLC (developing system, toluene-acetone; 1:1) to obtain 3 mg of the authentic (R)-form. The thus obtained authentic (R)-form compound showed the same residence time (14.0 minutes; moving phase 2.5% isopropanol/0.01M phosphate buffer (pH 7.1), flow rate: 0.8 ml/min) as that of the title compound obtained above on the column for optical resolution described above. With respect to the (S)-form, the residence time was 8.4 minutes under the same conditions.

Workup

  1. stirringby stirring for further 2 hours
  2. washthe mixture was washed with water
  3. dry with materialthe resulting organic layer was dried over anhydrous sodium sulfate
  4. distillationThe solvent was then distilled off
  5. customThe residue thus obtained
  6. customwas purified on a preparative silica gel TLC (developing system, toluene-acetone; 1:1)

Sources & evidence

ORD record
ord-ff68ed82d10d4f99af62c0ee3d3ed828
Source dataset
uspto-grants-1997_06
Patent number
US05635395

Reaction notes

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